Anti-entrenchment rules prevent governments from passing unrepealable legislation and ensure that subsequent governments are free to revisit the policy choices of the past. However, governments—and local governments in particular—have become increasingly adept at using private law mechanisms like contracts and property conveyances to make binding precommitments into the future. Simultaneously, courts and state legislatures in recent years have reduced the availability of core de-entrenching tools, like eminent domain, that have traditionally allowed governments to recapture policymaking authority from the past. These changes threaten to shift democratic power intertemporally. This Article develops a typology of mechanisms for public entrenchment through private law and private rights, as well as core anti-entrenchment protections embedded in the law. It then develops a framework for evaluating entrenchment concerns, comparing the costs of decreased flexibility against the benefits of increased reliance. Viewed through this framework, some recent changes in the law appear particularly problematic, from restrictions on eminent domain, to the rise of development rights, and creative forms of municipal finance like selling assets instead of incurring debt.